Ethyl Thioglycolate → HCID 89543486, 화합물

HRID 922779노트

반응식

HRID 922779 반응식
[N+:1](/[CH:4]=[CH:5]/[CH:6]1[CH2:8][CH2:7]1)([O-:3])=[O:2].[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:10][SH:11]>C1COCC1>[CH:6]1([CH:5]([S:11][CH2:10][C:9]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][N+:1]([O-:3])=[O:2])[CH2:8][CH2:7]1

참가 물질

4

반응물 2

HCID 12185Ethyl ThioglycolateHCID 14978083Cyclopropane, (2-nitroethenyl)-, (E)-

생성물 1

HCID 89543486HCID 89543486, 화합물수율 94.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(E)-(2-Nitrovinyl)cyclopropane (4-11, 750 mg, 6.63 mmol) was taken up in THF (20 mL). To this was added ethyl thioglycolate (0.88 mL, 7.98 mmol) then TEA (1.2 mL, 8.61 mmol) at rt. After stirring overnight the mixture was concentrated. The crude product was subjected to silica gel chromatography (40 g, 0-20% EtOAc/hexanes, 10 minute gradient) to afford ethyl 2-((1-cyclopropyl-2-nitroethyl)thio)acetate (4-12, 1.46 g, 94%) as a clear oil. 1H NMR (399 MHz, CDCl3): δ 4.73-4.58 (m, 2H); 4.21 (q, J=7.1 Hz, 2H); 3.34 (d, J=6.2 Hz, 2H); 2.93 (dt, J=9.9, 7.2 Hz, 1H); 1.30 (t, J=7.1 Hz, 3H); 1.00-0.90 (m, 1H); 0.69 (dd, J=8.0, 1.6 Hz, 2H); 0.47-0.36 (m, 2H).

후처리

  1. customat rt
  2. concentrationwas concentrated
  3. customwas subjected to silica gel chromatography (40 g, 0-20% EtOAc/hexanes, 10 minute gradient)

출처 및 근거

ORD 기록
ord-e7652e7abd3d4b5c8cccbcda51d4bdbf
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278960B2

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